JP2000026362A - Production of alkaline-earth metal salt of beta-diketo compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an alkaline-earth metal salt of a β-diketo compound, prevent a resin from becoming high viscosity, useful as a nontoxic stabilizer in molding vinyl chloride resin, and having high quality and high stability by reacting an alkaline-earth metal compound with an aliphatic β-diketo compound. SOLUTION: This alkaline-earth metal salt of a β-diketo compound is obtained by reacting 1 mol particulate alkaline-earth metal compound (pref. calcium hydroxide, magnesium hydroxide, or the like) with >=2.04 mol aliphatic β-diketo compound added continuously or intermittently at the maximum temperature of >=50 deg.C, drying the reactional mixture at 100-180 deg.C pref. in an inert gas atmosphere and by aging it. It is pref. that the β-diketo compound is a compound of the formula (R1 and R2 are each H, a 1-6C alkyl, or the like), e.g. an acetoacetic (1-4C) ester or acetylacetone, and the alkaline-earth metal salt of the β-diketo compound has <=1 wt.% moisture content and >=98.0% purity.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an alkaline earth metal salt of a .beta.-diketo compound used as a resin molding aid and a method for producing the same.

[0002]

2. Description of the Related Art Alkaline earth metal salts of β-diketo compounds (hereinafter referred to as β-diketo compound salts) are used as non-toxic stabilizers for molding resins, especially for molding vinyl chloride resins.

Various methods are known for producing salts of β-diketo compounds. For example, Zh. Neorg. Khim.
(1990), 35 (11), 2776-80, with acetylacetone,
By reaction with calcium chloride or calcium nitrate, β
-A method for obtaining a diketo compound salt is disclosed. However, in this method, impurities such as chlorides and nitrates are mixed in the obtained β-diketo compound salt (acetylacetonate), and it is necessary to remove the impurities, which is disadvantageous in quality.

Japanese Patent Publication No. 24777/1985 discloses that an equivalent (2 mol) of a β-diketo compound is used per 1 mol of an alkaline earth metal hydroxide, A method for producing a β-diketo compound salt to which a metal hydroxide is added is described. However, this method increases the viscosity in the latter half of the reaction and increases the power load on the stirrer. Therefore, an expensive reactor is required, which is industrially disadvantageous. Further, the obtained β-diketo compound contains about 6 to 7% by weight of water (corresponding to one molecule of water of crystallization), and thus is not suitable for use as a stabilizer. For example, in the case of molding a vinyl chloride resin, if a stabilizer containing water of crystallization is used, foaming due to water vapor occurs, so that the strength and transparency of the vinyl chloride resin are greatly reduced. Furthermore, the β-diketo compounds obtained by the method of this document have low stability and cannot be stored for a long time. For example, when the calcium salt of acetylacetone obtained by this method is dried to a moisture content of 1% by weight or less,
The purity greatly decreases from 97% by weight to 86% by weight in a month.

[0005] Also, German Patent DE 96-196103.
No. 20, the β-diketo compound is used in an equivalent amount (2 mol) to 1 mol of the alkaline earth metal hydroxide, and the β-diketo compound is added to the alkaline earth metal hydroxide in the absence of a solvent. A method for producing a β-diketo compound salt to which (eg, acetylacetone) is added is described. In the method of this document, a β-diketo compound is added to an alkaline earth metal hydroxide and reacted at a temperature of 40 ° C. or less, whereby the reaction mixture can be prevented from becoming highly viscous, and the reaction mixture can be obtained in a powdery state. Can react. However, in the method of this document, the reaction takes a long time to complete, the conversion is low (for example, about 94% when slaked lime is used), and the obtained β-diketo compound salt is also low in purity. is there.

[0006]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a high-quality and highly stable β-diketo compound salt and a method for producing the same. Another object of the present invention is to suppress the increase in viscosity and suppress the increase in viscosity while reacting in the form of powder and granules, to industrially produce a β-diketo compound salt having high conversion and high purity. It is to provide a method that can be manufactured.

[0007]

Means for Solving the Problems The inventors of the present invention have considered that if unreacted alkaline earth metal hydroxide such as calcium hydroxide remains, the acetylacetone unit of the β-diketo compound salt is condensed. It was found that the purity of the β-diketo compound salt was greatly reduced. The present inventors have made intensive studies based on these findings to achieve the above object, and as a result, when an excess amount of the aliphatic β-diketo compound is used relative to the alkaline earth metal compound, the β
-The diketo compound salt was found to be high in purity and high in stability, and completed the present invention.

That is, the present invention is a method for producing an alkaline earth metal salt of a β-diketo compound from a granular alkaline earth metal compound and an aliphatic β-diketo compound,
The aliphatic β-diketo compound is used in an amount of 2.04 mol or more per 1 mol of the alkaline earth metal compound. The alkaline earth metal compound and the aliphatic β-diketo compound may be reacted while being supplied continuously or intermittently, and may be used for one of the alkaline earth metal compound and the aliphatic β-diketo compound. The other component may be added continuously or intermittently. The maximum temperature of the reaction may be 50 ° C or higher, and the drying may be performed at a temperature of 100 to 180 ° C in an inert gas atmosphere. The alkaline earth metal compound may be calcium hydroxide, magnesium hydroxide or barium hydroxide. The aliphatic β-diketo compound is represented by the following formula (1)

[0009]

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(Wherein R ¹ and R ² are the same or different and each represent a hydrogen atom, a C _1-6 alkyl group or a C _1-10 alkoxy group). It may be a C _1-4 alkyl acetoacetate or acetylacetone.

The alkaline earth metal salt of the β-diketo compound of the present invention can be obtained by the above method. The alkaline earth metal salt of the β-diketo compound has a water content of 1% by weight or less and a purity of 98.0% by weight or more.

[0012]

DESCRIPTION OF THE PREFERRED EMBODIMENTS [Alkaline earth metal compound] Examples of the alkaline earth metal compound include hydroxides of alkaline earth metals (eg, magnesium hydroxide, calcium hydroxide, barium hydroxide). These alkaline earth metal compounds can be used alone or in combination of two or more.

The alkaline earth metal compound can be used in the form of a powder. As the alkaline earth metal compound, those commercially available for industrial use may be used as they are, and the average particle diameter of the alkaline earth metal compound is about 0.1 to 300 μm, preferably 0.1 to 150 μm. It is about.

Further, as the alkaline earth metal compound,
It is preferable that it contains almost no impurities (silica, alumina, alkaline earth metal carbonate, etc.). The content of impurities is, for example, 2% by weight or less, preferably 1% by weight or less, and more preferably 0.5% by weight or less.

[Aliphatic β-diketo compound] As the aliphatic β-diketo compound, the compound represented by the above formula (1) can be used. In the formula (1), R ¹ and R ² are the same or different and are each a hydrogen atom, a C _1-6 alkyl group (for example,
A C _1-4 alkyl group such as a methyl group or an ethyl group) or C
_1-10 alkoxy group (for example, methoxy group, ethoxy group,
C _1-6 alkoxy groups such as propoxy and butoxy groups)
And, for example, a compound having a 2,4-alkanedione structure or an acetoacetic ester structure can be exemplified.

Preferred aliphatic β-diketo compounds
Is represented by the formula (1)¹Is C _1-4Alkyl group
(Methyl group, ethyl group, etc.), R^TwoIs C_1-4Alkyl group
(Methyl group, ethyl group, etc.) or C_1-6Alkoxy group
(Methoxy group, ethoxy group, propoxy group, butoxy group
And the like). Note that R¹And R
^TwoIs at the same time C_1-4Even when it represents an alkyl group, R
¹And R^TwoBut different C_1-4It may represent an alkyl group.
Particularly preferred aliphatic β-diketo compounds include acetyl
Seton, acetoacetic acid C_1-4Alkyl ester (aceto vinegar
Acid, ethyl acetoacetate, etc.).

As the aliphatic β-diketo compound, those commercially available for industrial use can be used as they are.

In the present invention, for the alkaline earth metal,
By using an excess amount of the aliphatic β-diketo compound, a highly pure and highly stable β-diketo compound salt can be obtained regardless of the reaction method. That is, in the present invention, 1 mol of the alkaline earth metal compound is
-A diketo compound in an amount of 2.04 moles or more, for example, 2.
About 04 to 5 mol (for example, about 2.05 to 4.5 mol), preferably about 2.1 to 4 mol (for example, 2.1
To about 3 mol), more preferably about 2.2 to 2.8 mol (particularly about 2.2 to 2.6 mol). By using the aliphatic β-diketo compound slightly more than 2 mol, the residual amount of the alkaline earth metal compound can be greatly reduced, and the purity and stability of the β-diketo compound salt can be improved. If the amount of the aliphatic β-diketo compound used is too large, the viscosity of the reaction mixture becomes large (kneaded) near the end of the reaction, and stirring becomes difficult.

[Reaction] In the present invention, a β-diketo compound salt can be produced by reacting an alkaline earth metal compound with a β-diketo compound while maintaining the fluidity of the granular material.

The reaction between the alkaline earth metal compound and the β-diketo compound can be carried out by continuously or intermittently supplying the alkaline earth metal compound and the aliphatic β-diketo compound to the reactor. For example, a reactor capable of mixing and stirring an alkaline earth metal compound and a β-diketo compound from an addition device (such as a quantitative supply device) (for example, a kneader,
The reaction can be carried out by supplying the powder to a stirring and mixing device for powder such as a groove type drier or a ribo blender.

Further, the reaction may be carried out by continuously or intermittently adding one of the alkaline earth metal compound and the aliphatic β-diketo compound to the other component. In addition, even if an alkaline earth metal compound is continuously or intermittently added to a β-diketo compound, a highly stable and highly stable β-diketo compound salt can be produced, but the viscosity of the reaction mixture increases in the latter half of the reaction. There are cases. Therefore, it is advantageous to react the alkaline earth metal compound by continuously or intermittently adding the aliphatic β-diketo compound. The method of adding the aliphatic β-diketo compound has the advantage that the powder state of the mixture can be maintained in all steps from the reaction to the drying.

As a method for adding the β-diketo compound, for example, a stirring and mixing reactor (eg, a powder mixer such as a kneader, a groove dryer, a ribbon blender, etc.) may be used.
(A device having mixing capability), a method of charging a granular material of an alkaline earth metal hydroxide, and continuously or intermittently adding an aliphatic β-diketo compound while stirring the granular material.

Since the reaction between the alkaline earth metal compound and the aliphatic β-diketo compound is an exothermic reaction, the reaction is usually carried out by removing the heat of reaction by cooling (eg, jacket cooling) and controlling the reaction temperature. The reaction temperature is, for example, about 0 to 100 ° C, preferably about 30 to 100 ° C, and more preferably about 60 to 80 ° C. When the reaction temperature exceeds 100 ° C., the conversion of the alkaline earth metal compound becomes low due to the loss of the aliphatic β-diketo compound, so that the quality (color, purity, stability, etc.) of the obtained β-diketo compound salt is reduced. descend.

In the reaction step, the maximum temperature during the reaction is:
It is preferable to control the temperature to 50 ° C. or higher (for example, about 50 to 100 ° C.) and 55 ° C. or higher (for example, about 55 to 95 ° C., particularly about 55 to 80 ° C.). When the maximum temperature during the reaction is 50 ° C. or higher, the conversion of the alkaline earth metal compound can be improved, and the purity and stability of the resulting β-diketo compound salt can be improved. The reaction can be performed in a batch system, semi-batch system or continuous system.

[Aging] The reaction mixture obtained by the batch system or the semi-batch system may be aged, if necessary. The aging can further increase the conversion of the alkaline earth metal compound. The aging temperature is, for example, 40 to 100 ° C.
Degree, preferably about 50 to 90 ° C, more preferably about 60 to 80 ° C. When the aging temperature is higher than 100 ° C., the quality (color, purity, stability, etc.) of the resulting β-diketo compound salt is reduced due to loss of the aliphatic β-diketo compound.
Decrease.

The aging time can be appropriately selected and is usually 1 hour or more, preferably 1 to 24 hours (for example, 1 to 16 hours).
Degree, more preferably about 4 to 12 hours,
It may be about 8 hours.

[Drying] The reaction mixture is usually used as a reaction by-product water (for example, 2 mol of water is by-produced for 1 mol of slaked lime).
And water of crystallization. For this reason, the β-diketo compound salt can be obtained by drying the reaction mixture directly or after completion of aging and removing the reaction by-product water and the water of crystallization.

Drying can be performed in an inert gas (nitrogen, helium, carbon dioxide, etc.) atmosphere, preferably in an inert gas stream (for example, while blowing the inert gas into the reactor). When dried under an air atmosphere, the product is colored by oxidation and condensation of the β-diketo compound. In addition,
If necessary, drying may be performed under reduced pressure.

The drying temperature (for example, when the temperature is raised, the ultimate temperature of drying) is usually about 100 to 180 ° C., preferably about 100 to 150 ° C. (for example, 120 to 15 ° C.).
(About 0 ° C.). If the drying temperature is lower than 100 ° C., it is difficult to remove water of crystallization. The drying temperature may be selected according to the type of the β-diketo compound salt as long as the β-diketo compound salt is not decomposed. Table 1 shows preferred drying temperatures for representative β-diketo compound salts.

[0030]

[Table 1]

By drying, the aliphatic β-diketo compound used in excess can be removed from the β-diketo compound salt. The removed aliphatic β-diketo compound can be condensed and collected together with the by-product water with a condenser or the like, and can be used again for the reaction with the alkaline earth metal compound.

The drying may be carried out in the above-mentioned reactor, or separately in a batch system, a semi-batch system or a continuous system.

The β-diketo compound salt thus obtained has a high purity and is usually at least 98.0% by weight.
The water content is 1% by weight or less, preferably 0.1% by weight.
8% by weight or less, more preferably 0.5% by weight or less, usually about 0.1 to 0.8% by weight (particularly 0.1 to 0.8% by weight).
0.5% by weight). Further, the content of impurities is 2% by weight or less, preferably 1.8% by weight or less, more preferably 1.5% by weight or less, and usually 0.1 to 10% by weight.
It is about 1.8% by weight (particularly about 0.1 to 1.5% by weight). Since the content of impurities is small, the β-diketo compound salt of the present invention has high stability.

The β-diketo compound salt of the present invention can be used as a stabilizer for vinyl chloride resins. Particularly, since the water content is small, it can be used as a low foaming stabilizer. Also,
Since it has high stability, it can be used stably for a long period of time.

[0035]

According to the present invention, the content of the alkaline earth metal in the β-diketo compound salt can be reduced, so that a high-quality and stable β-diketo compound salt can be obtained. Further, a β-diketo compound salt having a high conversion and a high purity can be industrially advantageously produced.

[0036]

The present invention will be described below in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.

Comparative Example 1 Into a 3 L kneader equipped with a thermometer, a dropping funnel, a condenser and a jacket, 1202 g (1
2.0 mol) and stirred, and 444 g of calcium hydroxide was added.
[6 mol, calcium hydroxide / acetylacetone = 1 /
2.0 (molar ratio)] over 3 hours. Reaction temperature was 32-65C. After dropping, the temperature is 65-68.
The mixture was stirred and mixed at 4 ° C. for 4 hours to complete the reaction. The mixture was heated under a stream of nitrogen gas, and when the temperature reached 68 ° C., the drying process was started. After cooling, 1550 g of yellow-white calcium acetylacetone [99.1 mol% yield]
(Based on calcium hydroxide), purity 91.5% by weight].

Comparative Example 2 Calcium acetylacetone 400 obtained in Comparative Example 1
g in a hot air dryer at 120 ° C. for 16 hours.
76 g (water 0.6% by weight, purity 97.6% by weight) were obtained.

Comparative Example 3 Calcium hydroxide 444 was added to the kneader used in Comparative Example 1.
g (6 mol) was added and stirred. Temperature below 40 ° C (3
Acetylacetone 1202
g [12.0 mol, calcium hydroxide / acetylacetone = 1 / 2.0 (molar ratio)] was added dropwise over 6 hours.
After the completion of the dropwise addition, while passing nitrogen gas (50 L / hr),
The reaction was terminated by further stirring for 40 minutes. The whole reaction product (1683 g) was transferred to a rotary evaporator,
It dried under reduced pressure (30 Torr) at 80 ° C. for 36 hours while passing nitrogen gas (5 L / hr). After the start of drying, 2
In 4 hours, the water content decreased to 6.3 to 6.4% by weight.
After that there was little change. After cooling, 1540 g of acetylacetone [yield 98.7 mol% (based on calcium hydroxide), water content 6.3 wt%, purity 91.7 wt%] was obtained.

Comparative Example 4 Calcium acetylacetone 600 obtained in Comparative Example 1
g with a rotary evaporator and aerated with nitrogen (5 L).
/ Hr) and reduced pressure at 120 ° C for 8 hours (30 Torr)
After drying, 563 g of powder or granules (water 0.1% by weight, purity 9)
7.7% by weight).

Example 1 Calcium hydroxide 444 was added to the kneader used in Comparative Example 1.
g (6 mol), stirred, and acetylacetone 132
0 g [13.2 mol, calcium hydroxide / acetylacetone = 1 / 2.2 (molar ratio)] was added dropwise over 3 hours. The reaction temperature was 43-65 ° C. After completion of the dropwise addition, the mixture was stirred and mixed at a temperature of 65 to 66 ° C. for 4 hours to complete the reaction. The resulting powder had some moisture. While heating in a nitrogen gas stream, the process was shifted to a drying step when the temperature reached 68 ° C, and at a temperature of 106 to 138 ° C and a water content of 0.1.
Dried for 10 hours to 46% by weight. After cooling, 1425 g of white calcium calcium acetylacetone [yield 98.
2 mol% (based on calcium hydroxide), purity 98.6% by weight].

Example 2 Magnesium hydroxide 350 was added to the kneader used in Comparative Example 1.
g (6 mol) was added and stirred, and acetylacetone 144 was added.
3 g [14.4 mol, magnesium hydroxide / acetylacetone = 1 / 2.4 (molar ratio)] was added dropwise over 3 hours. Reaction temperature was 35-64 ° C. After completion of the dropwise addition, the mixture was stirred and mixed at a temperature of 64 to 65 ° C. for 4 hours to complete the reaction. While heating under a nitrogen gas stream, the process proceeds to the drying step when the temperature reaches 65 ° C., and the temperature is 104 to 125 ° C.
And dried for 12 hours until the water content became 0.17% by weight.
After cooling, white magnesium acetylacetone 1342
g [yield 99.3 mol% (based on magnesium hydroxide);
(Purity: 98.9% by weight).

The distillate at the time of drying was separated into two layers, and 232 g of acetylacetone containing 5.3% by weight of water was recovered from the upper layer.

Example 3 444 g of calcium hydroxide was added to the kneader used in Comparative Example 1.
(6 mol), and stirred.
g [13.2 mol, calcium hydroxide / methyl acetoacetate = 1 / 2.2 (molar ratio)] was added dropwise over 3 hours.
The reaction temperature was 36-58 ° C. After completion of the dropwise addition, the mixture was stirred and mixed at a temperature of 58 to 62 ° C for 5 hours to complete the reaction. While heating under a nitrogen gas stream, the process was shifted to a drying step when the temperature reached 62 ° C., and a temperature of 110 to 122 ° C.
And dried for 18 hours until the water content became 0.65% by weight. After cooling, white methyl calcium acetoacetate 161
8 g [yield 97.9 mol% (based on calcium hydroxide),
Purity: 98.1% by weight].

Example 4 444 g of calcium hydroxide was added to the kneader used in Comparative Example 1.
(6 mol), stirred, and acetylacetone 1102 was added.
g and 230 g of acetylacetone recovered in Example 2 [total 1332 g, 14.4 mol, calcium hydroxide / acetylacetone = 1 / 2.2 (molar ratio)] were added dropwise over 3 hours. The reaction temperature was 46-67 ° C. After completion of the dropwise addition, the mixture was stirred and mixed at a temperature of 64-68 ° C for 4 hours to complete the reaction. While heating in a nitrogen gas stream, the temperature is 6
When the temperature reaches 6 ° C., the process proceeds to the drying process,
It was dried at 125 ° C. for 12 hours until the water content became 0.44% by weight. After cooling, 1435 g of white calcium acetylacetone (98.5 mol% (based on calcium hydroxide), purity 98.2% by weight) was obtained.

The distillate at the time of drying was separated into two layers, and acetylacetone 1 containing 5.1% by weight of water was separated from the upper layer.
11 g were collected.

Example 5 A 50 L conicer equipped with a liquid and powder metering device and a jacket was connected to a solit air dryer equipped with a receiving tank, a bag filter and a condenser.
A test device was manufactured. From the metering device to the co-kneader,
Calcium hydroxide was supplied at a feed rate of 3.7 kg / hr (50 mol / hr), and a feed rate of 11.0 kg / hr [11
0 mol / hr, calcium hydroxide / acetylacetone =
1 / 2.2 (molar ratio)], and the mixture was stirred and reacted while supplying acetylacetone. The reaction product was continuously supplied to a solit air dryer, and a jacket gas (158 L / hr) was introduced while passing nitrogen gas (100 L / hr).
C.) to dry continuously.

When the above continuous operation (reaction temperature 81-92 ° C.) was continued for 5 hours, calcium acetylacetonate 5
9.4 kg [yield 98.2 mol% (based on calcium hydroxide), water content 0.46 wt%, purity 98.6 wt%] were obtained.

The distillate from the drying apparatus condensed in the condenser was 11.7 kg (4.8 kg of the upper liquid, 6.9 kg of the lower liquid), and the upper liquid was acetylacetone 94.
It contained 9% by weight and 4.6% by weight of water.

Example 6 Using the reactor used in Example 5, the feed rate was 3.7 kg / hr (50 mol / h) from the quantitative feeder to the co-kneader.
r) calcium hydroxide at a feed rate of 14.0 kg
/ Hr [140 mol / hr, calcium hydroxide / acetylacetone = 1 / 2.8 (molar ratio)] while stirring and mixing while supplying acetylacetone to cause a reaction. The reaction product was continuously supplied to a solid air dryer, and continuously dried by heating with steam (161 ° C.) in a jacket while passing nitrogen gas (200 L / hr).

When the above continuous operation (reaction temperature 74-79 ° C.) was continued for 5 hours, calcium acetylacetonate 5
9.7 kg [yield 99.6 mol% (based on calcium hydroxide), water content 0.17 wt%, purity 99.5 wt%] were obtained.

The distillate condensed in the condenser from the drying device was 19.0 kg (20.8 kg of the upper liquid, 8.2 kg of the lower liquid), and the upper liquid was acetylacetone 9
It contained 4.5% by weight and 5.2% by weight of water.

The calcium acetylacetone obtained in Examples 1, 5, 6 and Comparative Examples 1-4 was sealed in a container and stored at a temperature of 25 ± 1 ° C. and a humidity of 75 ± 2%.
The stability was investigated. The stability was evaluated by the change over time in the purity of acetylacetone (from the start of sealing to after 12 months).
Table 2 shows the results.

[0054]

[Table 2]

As is clear from Table 2, the calcium acetylacetonate of the examples has high stability even after long-term storage, and can maintain almost the original purity.

Example 7 Using the reactor used in Example 5, the feed rate was 3.7 kg / hr (50 mol / h) from the quantitative feeder to the co-kneader.
r) calcium hydroxide at a feed rate of 13.9 kg
/ Hr [120 mol / hr, calcium hydroxide / methyl acetoacetate = 1 / 2.4 (molar ratio)] while mixing and stirring while supplying methyl acetoacetate. The reaction product was continuously supplied to a solid air dryer, and continuously dried by heating with steam (143 ° C.) in a jacket while passing nitrogen gas (100 L / hr).

When the above continuous operation (reaction temperature 82-91 ° C.) was continued for 5 hours, methyl calcium acetoacetate 6
7.7 kg [yield 98.6 mol% (based on calcium hydroxide), water content 0.61 wt%, purity 98.5 wt%] were obtained.

The distillate from the drying device condensed in the condenser was 18.4 kg (without layer separation) and contained 62.8% by weight of methyl acetoacetate and 36.6% by weight of water.

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Claims (13)

[Claims] 1. A method for producing an alkaline earth metal salt of a β-diketo compound from a granular alkaline earth metal compound and an aliphatic β-diketo compound, wherein 2.0% of the aliphatic β-diketo compound
A method for producing an alkaline earth metal salt of a β-diketo compound used in an amount of 4 mol or more. 2. The production method according to claim 1, wherein the alkaline earth metal compound and the aliphatic β-diketo compound are reacted while being supplied continuously or intermittently. 3. An alkaline earth metal compound and an aliphatic β-
2. The production method according to claim 1, wherein the other component is added continuously or intermittently to one component among the diketo compounds. 4. The method according to claim 1, wherein the β-diketo compound is continuously or intermittently added to the alkaline earth metal compound. 5. The method according to claim 1, wherein the maximum temperature of the reaction between the alkaline earth metal compound and the aliphatic β-diketo compound is 50 ° C. or higher. 6. The method according to claim 1, wherein the reaction mixture is dried at a temperature of 100 to 180 ° C. in an inert gas atmosphere. 7. The method according to claim 1, wherein the reaction mixture is aged. 8. The method according to claim 1, wherein the alkaline earth metal compound is calcium hydroxide, magnesium hydroxide or barium hydroxide. 9. An aliphatic β-diketo compound represented by the following formula (1): (Wherein R ¹ and R ² are the same or different and represent a hydrogen atom, a C _1-6 alkyl group or a C _1-10 alkoxy group)
The method according to claim 1, which is a compound represented by the formula: 10. The method according to claim 1, wherein the aliphatic β-diketo compound is C _1-4 acetoacetate or acetylacetone.
The manufacturing method as described. 11. A method for producing an alkaline earth metal salt of a β-diketo compound by continuously or intermittently adding an aliphatic β-diketo compound to a granular alkaline earth metal compound, comprising: Production of alkaline earth metal salt of β-diketo compound by drying at a temperature of 100 to 150 ° C. under an inert gas atmosphere using 2.1 to 3 moles of aliphatic β-diketo compound per 1 mol of earth metal compound Method. 12. A water content of 1% by weight or less and a purity of 98.
0% by weight or more of an alkaline earth metal salt of a β-diketo compound. 13. β obtained by the method according to claim 1.
-Alkaline earth metal salts of diketo compounds.